The reaction of 2-chloro-4-nitrophenol and the isomeric chloronitrobenzenes with LDA under aryne-forming conditions
S Tandel, A Wang, TC Holdeman, H Zhang, ER Biehl
Index: Tandel, Sagun; Wang, Anlai; Holdeman, Terra C.; Zhang, Hongming; Biehl, Edward R. Tetrahedron, 1998 , vol. 54, # 50 p. 15147 - 15154
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Citation Number: 6
Abstract
The unprecedented base-initiated generation of a nitrobenzyne and subsequent addition of preformed arylacetonitrile anion nucleophiles is reported. In all cases, 2-amino-5-nitro-3- benzo [b] furans are obtained as major product with small amounts of 3-arylmethyl-2-cyano- 4-nitrophenols. A mechanism involving ring closure of phenoxide and nitrile groups of the initial aryne-nitrile anion adduct is proposed to account for the formation of the ...
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